Вы находитесь на странице: 1из 26

Organic Chemistry UNIT 2

Section A : Straight Objective Type


1. Answer (4)

Br

* *
I * * Cl

2. Answer (3)
Electron withdrawing group increases rate for SN reactions.
3. Answer (4)
Number of stereoisomers = 2n (n = number of asymmetric carbon atoms + number of double bonds)

3a. Answer (1, 4) (IIT-JEE 2009)


Given compound has three stereocentre with symmetrical substituents. It will form six stereoisomers out
of which 2 will be meso and one dl pair of cis and one dl pair of trans.

4. Answer (1)
Meso tartaric acid is optically inactive due to presence of plane of symmetry.
5. Answer (1)

CH3 CH3

The Fisher projection of the compound is HO H and it has R & R configuration on both

H OH
asymmetric C-atom.
6. Answer (2)
7. Answer (1)

CH2CH2Cl CHClCH3 CH2Cl CH2Cl CH2Cl


CH3

CH3
CH3

8. Answer (1)
9. Answer (4)
: CCl2 can function as an electrophile but not as a nucleophile.
10. Answer (4)

Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
64 Organic Chemistry Success Magnet -Solutions (Part-II)

11. Answer (2)

11(a). Answer (1, 2, 3) (IIT-JEE 2012)


With reference to structure (M), if the chiral carbon bearing the methyl group is C–1 and that bearing the
chlorine is C–2 then

Structure Configuration of C–1, C–2


respectively

M S, R
N R, R
O S, R
P R, S
Q R, R
Now from the above configurations we learn that
(1) M and N are diastereomers i.e., non-mirror image stereoisomers.
(2) M and O are surely identical as their configurations are same.
(3) M and P are also enantiomers due to opposite configurations.
But M and Q are again not identical but diastereomeric.
Hence answer is (1, 2, 3).

12. Answer (2)


Ketal formation.
13. Answer (4)

1 , 2 and 3 has plane of symmetry.


14. Answer (3)
In ortho substituted amines, nitrogen moves out of the plane.
15. Answer (3)
Stronger base has lesser value of pKb.
16. Answer (2)
–OH group of molecule will behave as a basic site in presence of HCl.
17. Answer (2)
CH3 CH3
H H2
C—C—C—C CH = CH – C
CH3 CH3 CH
H C – CH3 H
H CH – CH3
(optically inactive)
Triple bond is more sensitive for addition H2 than double bond.
18. Answer (1)

cis trans

For rings having  10C atoms cis alkenes more stable than trans.

Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Success Magnet -Solutions (Part-II) Organic Chemistry 65
19. Answer (4)

Cl
Cl Cl Cl
Cl
, , , Cl
Cl
Cl

20. Answer (2)

C2H5Br
CH3 – C  CNa CH3 – C C – C H2 – CH3

21. Answer (2)


Thiophene undergoes electrophilic substitution at 2nd position.
22. Answer (3)
Carbocation formation and ring expansion takes place.
23. Answer (3)

O O OH OH
O3 Li AlH4 ⎛ Chiral centre = 2 ⎞
CH3 – C  C – CH2CH3 CH3 – C – C – C2H5 CH3 – C – C – C2H5 ⎜⎝ Stereoisomer = 4 ⎟⎠
H H

24. Answer (4)

THF
R – CH = CH2 + BH3 R – CH – CH2

H B–H

H
2R – CH = CH2

NH2Cl/H2O
R – CH2 – CH2 – NH2 (R – CH2 – CH2)3B

25. Answer (1)

1  Kolbe’s electrolytic reaction.

26. Answer (4)


  
NaNH2 CH
CH3  C  C H   CH3  C  C Na 
3
 CH3  C  C  CH3

27. Answer (3)


Williamson’s synthesis.
28. Answer (1)
Retention is dominating over inversion.
29. Answer (3)
Saytzeff product.

Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
66 Organic Chemistry Success Magnet -Solutions (Part-II)

30. Answer (3)

HBr H Br

Br
Br Br

31. Answer (3)

Anti-aromatic

32. Answer (2)


H
Cold OH
KMnO4/OH– H
OH
+ Syn hydroxylation
Peracid/H3O

OH
OH
H
anti-hydroxylation

33. Answer (2)


Cl NH2 NH2
NH2 NH2 HNH2
– NH3 – NH2 .
Cl Cl Cl Cl
Benzyne

34. Answer (4)

aq KOH
C2H5OH
C2H5Br (1)
alc
CH2 = CH2
(2)

C2H5OH and CH3OCH3 are isomers



H
C2H5OH 
 CH2  CH2 .

35. Answer (3)


– NO2 group is electron withdrawing it show –I & –R effect. More over it stabilize anion more than other group.
36. Answer (1)
Inversion product.

Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Success Magnet -Solutions (Part-II) Organic Chemistry 67
37. Answer (1)
– NO2 at ‘o’ and ‘p’ position stabilize anion

F F OH
NO2 NO2

+ OH
CH3 CH3
NO2 NO2

F OH
O2N – –

– CH3
NO2

38. Answer (1)



O O
C CH3 C + CH3
CH3 O CH3 O
39. Answer (1)
– NO2 group show – I & – R effect.
40. Answer (4)
I

+ I2 + HI .

41. Answer (3)


SN1 reaction carbocation formation.
42. Answer (2)
OH
Br AgOH Br
Br
.
Br
43. Answer (4)
Depends on formation of free radical

Br2
Isomeric monobrominated product
(1 eq)
h 

Br2
+
h

44. Answer (4)


Carbene formation then ring expansion takes place.

Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
68 Organic Chemistry Success Magnet -Solutions (Part-II)

45. Answer (1)


Due to presence of benzylic group

CH2Cl NaOH CH2OH

Cl Cl
46. Answer (3)
O

CH3O CH2 – CH2 H2O/H


+

CH3CH2SH CH3CH2S CH3CH2–S–CH2–CH2O CH3CH2–S–CH2–CH2OH .


– CH3OH C
47. Answer (3)
SN1  involves cyclic formation and
–
R–O + O
R S=O R – Cl + SO2
S=O
Cl Cl

CH3
Where R = C .
H D
48. Answer (4)

Br


OH

OH O O
H
H

O O
H

49. Answer (4)

H + – H
Br Cl
CH3 – CH = C CH3 – CH – C – COOH
COOH
Cl Br
2 chiral carbon
2
2 =4
50. Answer (3)
4 4 2
2

2 4
2

Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Success Magnet -Solutions (Part-II) Organic Chemistry 69
51. Answer (1)

CH3
18
H2O
CH3 – C – CH2 +
H3C – C – CH2 Stable carbocation
O H
OH
18
H2 O

CH3 CH3
CH3 – C – CH2OH CH3 – C – CH2OH
18
O O 18
H H H
52. Answer (1)

(CH3 )3 C  Stable carbocation.


53. Answer (3)

H H
O O
O
N less stronger than
O
N O
O

Intramolecular H-bonding.
54. Answer (1)

O OH O
C  C
O + 2 O + H2O
C C

O H

OH OH
(phenolphthalein)
55. Answer (4)
56. Answer (3)
AgNO 3
R – O – R + HI  R – OH + RI    AgI ppt.
57. Answer (1)
Depends on electronegativity of elements and stability of conjugate pair.
58. Answer (3)
Due to presence of intramolecular H bonding in (a).
59. Answer (3)
60. Answer (3)
E1 Saytzeff oriented product.

Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
70 Organic Chemistry Success Magnet -Solutions (Part-II)

61. Answer (3)

+
OH OH2
+
+
H

H
+
+
+ –H

62. Answer (3)


Both NaBH4 and LiAlH4 reduces acid chloride to alcohols.
63. Answer (3)

OH

NO2 is weaker acid than H CO .


2 3

63(a). Answer (2, 4) (IIT-JEE 2012)


C6H5COOH + NaOH  C6H5COONa + H2O ; C6H5COOH + NaHCO3  C6H5COONa + CO2 + H2O
C6H5CH2 – OH + NaOH  No reaction ; C6H5CH2OH + NaHCO3  No reaction
C6H5CH2COOH + NaOH  C6H5CH2 – COONa + H2O ; C6H5CH2COOH + NaHCO3  C6H5CH2COONa
+ CO2 + H2O
C6H5CH2OH + NaOH  No reaction ; C6H5CH2OH + NaHCO3  No reaction

63(b). Answer (4) [JEE (Advanced)-2013]


Carbolic acid (Phenol) is weaker acid than carbonic acid and hence does not liberate CO2 on treatment
with aq. NaHCO3 solution. Benzoic acid, benzenesulphonic acid and salicylic are more acidic than
carbonic acid and hence will liberate CO2 with aq. NaHCO3 solution.

64. Answer (3)

OH

O — Fe — O
+ FeCl3 + HCl
O

(ferric phenoxide)
or (C6H5O)3Fe
H2O
[Fe(C6H5O)3(H2O)3]Cl3
Soluble complex

65. Answer (4)

Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Success Magnet -Solutions (Part-II) Organic Chemistry 71

65a. Answer (2, 3) [JEE (Advanced)-2017]


O O
(i) O3/CH2Cl2
CH3 CH3 C–H+H–C–H
(ii) Zn/H2O
Undergoes
Cannizzaro's
reaction
CH2 O O
O3/CH2Cl2
C C + H–C–H
Zn/H2O
CH3 CH3
Undergoes
Haloform reaction
O O
O3/CH2Cl2
CH3 C – H + CH3 – C – H
Zn/H2O

CH3 CH3 Undergoes


Cannizzaro's reaction
CH3
CH3 O CH3 CH3
O3/CH2Cl2
C +
Zn/H2O
CH3 O
CH3
CH3 Undergoes
Haloform reaction

66. Answer (1)


67. Answer (1)
Cl
|
Cl2  red P OH
CH3 — CH2 — CH2 — CH — COOH 
CH3 — CH2 — CH2 — CH2 — COOH  
OH
|
H /H2O CH3 — CH2 — CH2 — CH — COOH
CH3 — CH2 — CH2 — CH — COO  
|
OH
68. Answer (4)
+
H + +
OH
F
69. Answer (1)
NO2 NO2

+
+H (Stabilization by aromatisation and by NO2 group)

+
+H (Non-aromatic)

+
+H (Stabilization by aromatisation )

Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
72 Organic Chemistry Success Magnet -Solutions (Part-II)

70. Answer (2)

O CH2OH
+
H
CH3
OH
71. Answer (1)

O
O O
C – OH HO – CH2
+
C – OH HO – CH2
O O
O A

HO – CH2 O
H2SO4
CH2 
HO O

72. Answer (2)


73. Answer (1)
B is primary alcohol and C is secondary alcohol. Primary alcohol produces carboxylic acid and secondary
alcohol produces ketone.
74. Answer (2)

OH OH OH OH

CHCl3 CHO 50%KOH COOK CH2OH


+
KOH Cannizzaro
Reimer reaction
Tiemann
reaction

74a. Answer (4) [JEE(Advanced) 2014]


+ –
N2 Cl O H

O H O N N
NaOH

75. Answer (1)


OH
C6H5CO3H HBr
O
Br
(A) Trans 2-Bromocyclohexanol
76. Answer (4)

CH3 CH3
H2O
Compound -1 CH2 = CH – O – CH +
CH3CHO + CH3 – C – OH
CH3 H
H
Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Success Magnet -Solutions (Part-II) Organic Chemistry 73
CH3
H2O
Compound-2 CH2 = C – O – C2H5 +
CH3 – C – CH3 + C2H5OH
H
O
Both (1) & (2) gives same product.

76a. Answer (3) [JEE(Advanced) 2014]


–OCH3 group has +R effect. It increases the stability of the carbocation.

77. Answer (1)


O O

..
CH3 LDA or t-BuO /t-BuOH CH2
Br Kinetic enolate Br

SN2

78. Answer (4)


CH3OH < CH3 – O – CH3 < C6H5OH.
79. Answer (3)
Jone’s reagent oxidies 1° alcohol to aldehyde
CH2OH Jone's CHO
reagent
In choice (4), tertiary alcohol is resistant to oxidation at room temperature.

R – X + N a OR  R – O – R + NaX.
80. Answer (2)
Order of boiling point of isomeric alcohols 3° > 2° > 1°.
81. Answer (2)
O O

+ O O

O O
82. Answer (4)
Cross Cannizzaro reaction
HCHO is always oxidised to HCOOH other part reduced to alcohols.

82a. Answer (4) [JEE(Advanced) 2014]

O O– CH3
Cl Cl
CH3
CH3
O
CH3 – MgI

Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
74 Organic Chemistry Success Magnet -Solutions (Part-II)

83. Answer (1)


O
||
C  CH +
C — CH3 COONa
H I2 + NaOH
2+ + CHI3
Hg

84. Answer (1)

O CHO O COOH O CH2OH


KOH
+
50%

no ‘’ hydrogen atom


 Undergo Cannizzaro
85. Answer (3)

O
+
CH2 N N

+
CH2 N N O

O

O CF3CO3H

86. Answer (2)

CHO
5HIO4
(CHOH)4 5HCOOH + HCHO

CH2OH

87. Answer (2)


(A) Br is good leaving group and carbocation stabilize by allylic resonance.

(C) Nucleophilic attack fastest at CO due to presence of H.


88. Answer (3)
O
O
OH

OH
 (A)

O
(No elimination at bridge head carbon)
So, (1) gives positive DNP test.
89. Answer (2)
Only acid bromide and alkyl bromide undergo hydrolysis with alkali Br attached with benzene ring is resonance
stabilize therefore it give substitution at temperature and pressure.
Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Success Magnet -Solutions (Part-II) Organic Chemistry 75
90. Answer (4)

COOH
HO – CH2 – CH is most acidic so pH is low.
NH3

90(a). Answer (4) (IIT-JEE 2012)


When any group in R1 and R2 is basic group then amino acid is positively charged at pH = 7.0. So,
answers are peptide IV, VI, VIII and IX.

91. Answer (1)

O .. CH3
OH CH3 CH3 OCH3
..

..
CH3 H H CH3OH
..
.. O O O
OH
..
O O O O
92. Answer (3)
CH3
CH3MgI
CH3–CH2–CH2 – C N CH3 – CH2 – CH2 C = NMgI
+
H3O
CH3

CH3 – CH2 – CH2 – C = O


I
+ Mg
OH
93. Answer (4)
O O
H2S
CH3 – C – Cl CH3 – C – SH + HCl
[H – S – H]

94. Answer (4)


O
CH3 – C – O – CH3 + CH3 Mg Br

O MgBr O
H2O
CH3 – C – O – CH3 CH3 – C + Mg–Br + CH3OH
OH
CH3 CH3
(1) CH3MgBr
+
(2) H3O

OH

CH3 – C – CH3

CH3
95. Answer (3)

Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
76 Organic Chemistry Success Magnet -Solutions (Part-II)

96. Answer (4)


– +
O IC
I2
OH
– CHI3 +
O O

CH2I CHI2
In the above reaction and formed as intermediate products hence all ,
O O
O
CH2I CHI2
and give iodoform test.
O O
97. Answer (2)
CHO CH2 O H

CHO COO
NO2 NO2
OH

Conc. H2SO4 O
Conc. 
O
(Cannizaro
NO2 reaction) NO2
NO2
NO2
98. Answer (4)
99. Answer (2)
Br Br
Br2 Cl H2O OH
CH3 CH2 COOH PCl3
O O
100. Answer (2)

O O O
SOCl2 CH3OH
H – O – CH2 – C – OH Cl – CH2 – C – Cl Cl – CH2 – C – O–CH3

101. Answer (3)

O
CH3 CH2 C NH CH3
It should be noted that acid will be neutralised with amine.
102. Answer (1)
O O
OH
OH 
OH
+ CO2
O OH
OH
O O
Molar mass = Mg (M – 44)g

 O + H2O

O
(M – 62)g

Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Success Magnet -Solutions (Part-II) Organic Chemistry 77

102a. Answer (3) (IIT-JEE 2008)

O O O O
 I2 + NaOH
–CO2 C  C 
iodoform reaction
Ph  OH Ph CH3 Ph ONa + CHI3

-keto acid E G

103. Answer (4)


HIO4 can oxidise only two adjascent oxygen containing carbon atoms.
Aldehydic and 2° alcohol oxidise to formic acid whereas 1° alcohol to aldehyde by periodic acid.
104. Answer (2)

O O–H OH OH
+ –
H Br
+ (H – Br) H
Br Br
O O O OH

105. Answer (1)


Baeyers villiger oxidation.
106. Answer (3)

O NOH NH2

NH2OH Na/C2H5OH CH3


H

107. Answer (2)


HVZ followed by elimination.
108. Answer (3)
Ethylene glycol is protecting group for carbonyl.
109. Answer (3)
(A) NaBH4 reduces cabonyl group.
(B) HBO changes alkane to alcohol. (Anti-Markownikov’s product)
110. Answer (4)
Pinacol - pinacolone rearrangement.
111. Answer (2)

O O O
dil.
H2SO4 OH Tautomerize
OH
O OH O

H
Since compound does not have alcoholic group hence does not give victor meyer test.

Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
78 Organic Chemistry Success Magnet -Solutions (Part-II)

112. Answer (4)


Br MgBr

NBS Mg
dry ether

CH3CN

H3C – C = O H3C – C = N – MgBr

H2O

113. Answer (2)

In esterification higher the leaving aptitude of 'X' in R C X higher will be the rate of the reaction.
O
So, rate is highest in R C Cl .
O
114. Answer (1)
O

NH2 O H H – N – C – CH2Cl

+ Cl – C – C – Cl

H AlCl3

H
N
O or C=O
N CH2
H
115. Answer (1)
Coupling occurs prefenertially in the para position to the hydroxyl group. But it this position is blocked then
coupling occurs at ortho position.

115a. Answer (2) [JEE(Advanced)-2017]


OH OH O

NaNO2 + HCl aq.NaOH


0°C
+
NH2 N+  NCl– NN

OH O

N=N N=N H

Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Success Magnet -Solutions (Part-II) Organic Chemistry 79
116. Answer (3)

NO2 NO2 N2Cl Cl


Br2/FeBr3 NaNO2 Cu powder
HCl
Br Br Br
280 K (W)
(X) (Z)
Mg
Ether
Cl Cl
CH3
C6H5COCH3
C6H5 +
H3O
OH MgBr
(F) (A)

117. Answer (2)

NaNO2
NH2 HCl N2Cl
phenanthrene
118. Answer (1)

KCN SOCl2 H2/Pt NaOH


–HCl N
OH Cl OH CN Cl CN Cl CH2
H
NH2
119. Answer (2)

NH3 KOH CHCl3


 Br2 KOH
NH2 NC
O OH O NH2 C
A B +
H3O

(B & D  are same] + HCOOH


NH2 E
D

120. Answer (1)


F NMe2 NMe2 NMe2
(i) H2/Ni
Me2NH/DMF (ii) NaNO2/HCl H3PO2
Heat 0 – 5°C

NO2 NO2 N2Cl


121. Answer (1)
Hofmann elimination takes place, resulting the formation of less substituted alkene.

Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
80 Organic Chemistry Success Magnet -Solutions (Part-II)

122. Answer (1)

O
CH3 – C – H gives iodoform (haloform) test.
123. Answer (3)

O
C3H7
SOCl2 (CH3CH2CH2)2NH LiAlH4
CH3CH2COOH CH3CH2COCl CH3 – CH2 – C – N (C3H7)3N
A B C3H7 C

124. Answer (2)


Less substituted alkene is more stable


N CH3 OH— N CH2 + H2O
– H2O
CH3 CH3 CH3 CH3

125. Answer (3)

H H
CH3
C – NH2 + O = C – C – CH3
H3C
H CH3

H H
CH3
C – N = C – C – CH3
H3C
H CH3
H2/Pt

H
CH3 – C – N – CH2 – CH(CH3)2
CH3 H

126. Answer (1)

O
COOH O COOH O
COOH O
+ O
COOH COOH
COOH COOH COOH O

Two isomeric monoanhydrides

127. Answer (4)


Due to presence of +I effect of methyl group.
128. Answer (2)
Formation of quaternary ammonium salt.

Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Success Magnet -Solutions (Part-II) Organic Chemistry 81
129. Answer (1)
OH
OH N
+
O + H
N H
H

OH2
N
H

130. Answer (3)


Only benadryl is tertiary amine
Choline - quaternary ammonium salt
Benzedrine - primary amine
Coniine - secondary amine.
131. Answer (2)
2° amine react with Hinsberg reagent which forms insoluble material which does not soluble in NaOH.
1° amine react with Hinsberg reagent and finally form soluble complex. 3° amine does not react with Hinsberg
reagent.
132. Answer (2)

N–H

CH3I AgOH 
CH3 CH3
N – CH3 N I

I
CH3 CH3
AgOH CH3I excess
CH3 CH3
N – CH3  N

OH CH3
133. Answer (2)

H2O2
—N + N O

H
134. Answer (1)
O
O
C
OH
O + NH3
C NH2
C

O O

Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
82 Organic Chemistry Success Magnet -Solutions (Part-II)

135. Answer (1)

136. Answer (1)

OH OH
NO2 NO2
Conc. HNO3
Conc. H2SO4

NO2
Picric acid
OH OH
NO2 NO2
Conc. HNO3
Conc. H2SO4
OH OH
NO2
Styphnic acid
137. Answer (2)

NH2 NH2 NH2 NH2


NO2
HNO2 / H2SO4
+ +
NO2
NO2
(51%) (47%) (2%)

NH2 group is ortho-paradirecting in nature but during nitration in presence of H+, anillium ion is formed which is
metadirecting in nature.

138. Answer (1)

Br2/KOH HNO2
C2H5CONH2 C2H5NH2 CH3 CH2 + N2
(X) (Y) OH
Mustard oil
S C S I2/NaOH
reaction

C2H5 N C S CHI3 + HCOONa

139. Answer (3)


Basicity

N sp3 (localised lone pair) > N sp2 (localised lone pair) > N sp2 (delocalised lone pair)

139a. Answer (1) [JEE(Advanced)-2017]

NH2

H2N NH
IV
Resonance with two NH2 groups increases electron density on 'N' of NH

Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Success Magnet -Solutions (Part-II) Organic Chemistry 83

NH
Lesser increase of electron density on = NH due to
only one resonance with one –NH2
CH3 NH2
sp2
N

N This LPe is not available as it is involve in aromatic Sextet.
H 'N' is bonded to sp2 C on both sides.
III
N

N This LPe– is not involve in aromaticity. So more available


H 3
Also, 'N' is bonded to sp C on one side.
II
 IV > I > II > III

140. Answer (2)


NaBH4 reduces only carbonyl compound where as LiAlH4 reduces carbonyl and cyanide group.
141. Answer (3)
NH2
O NH3 OH

CH3
142. Answer (1)
O H O H
N O – N O
H–N OH N
H H
O H O H
O O
Anion (conjugate pair) stabilize by resonance.
143. Answer (1)
 
LiAlH4 H3O
CH3  C  N   CH3  CH2  NH2   CH3  CH2 NH3 .
144. Answer (2)
O
CH3
C = O + H2 N – NH2 – C – NH2
H
semi carbazide
Pyridine
O
H3C
C = N . NH – C – NH2
H
Semi carbazone
O

– NH2 of – C – NH2 does not undergo condensation due to its resonance stabilization.
O O

– C – NH2 – C = NH 2

Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
84 Organic Chemistry Success Magnet -Solutions (Part-II)

145. Answer (3)


1° amine oxidise to nitro group and 2° alcohol oxidise to ketone with cold KMnO4.
146. Answer (4)
NH2OH H2N–OH OH
O + O–H OH
H N – OH
Et OH
H H
– H2O

N–O–H N – OH

H
147. Answer (2)
NaOH react with carboxylic acid.
148. Answer (4)
3° amine cannot form amine oxide.
149. Answer (3)
Due to stability of carbocation.
150. Answer (2)
CH3
CH3 – CH2 – C – C = O + H2NCH3
H H

CH3 H
CH3 – CH2 – C – C = N – CH3
H
H2/Pt.

CH3 H H
CH3 – CH2 – C – C – N – CH3
H H
151. Answer (3)
Nylon has strongest intermolecular forces (i.e. hydrogen bonding) out of these.

151a. Answer (4) (IIT-JEE 2009)


In natural rubber polar groups are absent and hence it will have only weak van der Waals force of
attraction.

152. Answer (1)


Artificial silk is a polysaccharide while the other three are polyamides.
153. Answer (1)
CH3 CH3
CH3
n CH2 = C C – CH2 – C – CH2
CH3
CH3 CH3
154. Answer (2)

Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Success Magnet -Solutions (Part-II) Organic Chemistry 85
155. Answer (3)
⎛  ⎞
Amino acid are amphoteric in nature. The acidic properties are due to amino group ⎜⎜ – N H3 ⎟⎟ .
⎝ ⎠
156. Answer (1)
Alanine is NH 2 – CH – COOH

CH3
CH3 CH3
(At low pH) (At high pH) –
i.e. acidic pH NH3 – CH – COOH i.e. basic pH NH2 – CH – COO

157. Answer (1)


During vulcanization of natural rubber S – S crosslinks are formed which make it more elastic.
158. Answer (3)
343 K – 373 K, 6 – 7 atm
n CH2 = CH2 ( – CH2 – CH2 – )n
Ziegler – Natta catalyst
[TiCl4 + (C2H5 )3Al]
159. Answer (3)
The -helix is known as 3.613 helix since each turn of the helix has approximately 3.6 amino acids and 13
membered ring is formed by hydrogen bonding.
160. Answer (4)
Both insulin and carboxy peptidase contain Zinc.
161. Answer (3)
Cashmilon is polyacrylonitrile.
162. Answer (4)
COOH
Proline is heterocyclic amino acid. H – N H

 amino acid have a primary amino group except proline.


163. Answer (3)
Acrilan is PAN (Poly acrybonitrile).
164. Answer (4)
H
O
N
Caprolactum is monomer of Nylon-6 or Perlon

165. Answer (1)


OH

Bakelite is made up of (phenol) and HCHO (formaldehyde)

OH – OH –
H2C CH2
+ HCHO


CH2

Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
86 Organic Chemistry Success Magnet -Solutions (Part-II)

166. Answer (1)


Methoxy group is attached with carbonyl oxygen.
167. Answer (2)
There is a hydroxyl group and an ether attached to the same carbon forming a hemiacetal.
168. Answer (1)
OH group present on right side

H OH
CH2OH

168a. Answer (1) [JEE (Advanced)-2015]

CHO CHO
H OH HO H
HO H H OH
H OH HO H
H OH HO H
CH2OH Mirror CH2OH
D-(+)-glucose L-(–)-glucose

169. Answer (1)


Fat – 130 ATP, carbohydrate – 38 ATP, protein – 5 ATP.
170. Answer (1)

CH2OH
H O H
  – D – glucopyranose
OH H
OH OH
H OH
171. Answer (2)

CHO CH = NNHC6H5 CH = NNHC6H5 CH = NNHC6H5


C6H5NNH2 C6H5NNH2 C6H5NNH2
CHOH –H2O
CHOH –C6 H5NH2, – NH3
C=O –H2O
C = NNHC6H5

(CHOH)3 (CHOH)3 (CHOH)3 (CHOH)3

CH2OH CH2OH CH2OH CH2OH


glucosozone
172. Answer (2)
Only phospholipids form bilayer memberane.
173. Answer (2)

+ C6H12O6 C6H12O6
H
C12H12O11 + H2O invertase D(+)-glucose + D(–)-fructose
sucrose ( )D = 52.7 ( )D = –92.4°
( )D = +66.5°
invert ( )D = –19.9°

Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
Success Magnet -Solutions (Part-II) Organic Chemistry 87
174. Answer (3)

conc. HNO3 COOH


C12H22O11 + 18[O] + 5H2O
COOH
oxalic acid
175. Answer (2)
The excess glucose present in the blood is transported in the tissue where insulin converts it into glycogen.
The deficiency of insulin causes diabetis.
176. Answer (2)
Proteins give ninhydrin and molisch test.
177. Answer (4)
Fact
178. Answer (3)
The amino acid which cannot be synthesised in our body and must be obtained through diet are known as
essential amino acids.
e.g. Lysine, valine, histidine etc.
179. Answer (1)
Glucose and fructose have similar configuration on C3, C4 and C5 so they form same osazone. In osazone
only C1 and C2 are involved.
180. Answer (1)
181. Answer (1)
Thymine
In DNA
— Adenine
— Thymine
— Guanine
— Cytocine
In RNA Adenine is absent.
182. Answer (3)

183. Answer (3)


O H
peptide bond of protein form H–bond.
–C–N–
184. Answer (2)

Stearic acid, Palmatic acid and Oleic acid are higher fatty acids. Their Na salts are used as soaps.

185. Answer (2)

Chemical name of vitamin E is tocopherol.

186. Answer (3)

O C NH2 O C NH

OBr Br Br
–HOBr

Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456
88 Organic Chemistry Success Magnet -Solutions (Part-II)

O H O
C N Br C N Br

OBr

D2O
ND2 – O C N
OH
187. Answer (4)
Denaturation of protein converts quaternary, tertiary and secondary structure to primary structure.
188. Answer (2)
Invertase for carbohydrates, urease for urea and trypsin for protein.
189. Answer (4)

pH = 1 (acidic). It accepts a proton and exist as cation – NH3 is acidic group.
190. Answer (3)
Amide linkage (– CONH2)
191. Answer (4)
CH2OH
O
H * OH
5 Chiral carbon present in –D–glucose H
* OH H *
HO * * H

H OH
192. Answer (3)
CN
+ COOH
HCN H3O
H–C=O H – C – OH
(CHOH)5
(CHOH)4 (CHOH)4
CH2OH
CH2OH CH2OH
HI

COOH
(CH2)5

CH3
Heptanoic acid
193. Answer (3)
CH2OH

C= O

CH2OH
No chiral carbon
 No stereoisomers.
194. Answer (2)
Ruff degradation.
  
Aakash Educational Services Pvt. Ltd. Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005 Ph.011-47623456

Вам также может понравиться